(2S,4S)-Benzyl 4-methoxy-2-(pyrazin-2-ylcarbamoyl)pyrrolidine-1-carboxylate → (2S,4S)-4-Methoxy-N-(pyrazin-2-yl)pyrrolidine-2-carboxamide

HRID 1961383Notes

Reaction equation

HRID 1961383 reaction equation
[CH3:1][O:2][C@@H:3]1[CH2:7][N:6](C(OCC2C=CC=CC=2)=O)[C@H:5]([C:18](=[O:26])[NH:19][C:20]2[CH:25]=[N:24][CH:23]=[CH:22][N:21]=2)[CH2:4]1>CO.[Pd]>[CH3:1][O:2][C@@H:3]1[CH2:7][NH:6][C@H:5]([C:18]([NH:19][C:20]2[CH:25]=[N:24][CH:23]=[CH:22][N:21]=2)=[O:26])[CH2:4]1

Participants

4

Reactant 1

HCID 59436412(2S,4S)-Benzyl 4-methoxy-2-(pyrazin-2-ylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 59436335(2S,4S)-4-Methoxy-N-(pyrazin-2-yl)pyrrolidine-2-carboxamideYield 102.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2S,4S)-benzyl 4-methoxy-2-(pyrazin-2-ylcarbamoyl)pyrrolidine-1-carboxylate 18C (550 mg, 1.54 mmol) in methanol (200 mL) was added palladium on carbon (10%, 80 mg) under nitrogen. The suspension was hydrogenated at 55 psi overnight. The resulting suspension was filtered through a pad of celite and washed with methanol. Concentration of the filtrate gave the product (18D) as an oil (350 mg, 100%) which was used without purification in the next step. LC/MS [M+H]+: 223; Ret time (Method F): 0.76 min.

Workup

  1. customwas hydrogenated at 55 psi overnight
  2. filtrationThe resulting suspension was filtered through a pad of celite
  3. washwashed with methanol

Sources & evidence

ORD record
ord-2da1160e8b3c4a819b1b2ed5ef46e425
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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